Water-insoluble azo-dyestuffs



Patented Oct. 8, 1935 UNITED STATES PATENT OFFICE 2,016,495 WATER-INSOLUBLE AZO-DYESTUFFS Hans Heyna and Hans Huber, Frankfort-on-the- Main, Germany, assignors to General Aniline Works, Inc, New York, N. Y., a corporation of Delaware No Drawing. Application June 20, 1934, Serial No. 731,534. In Germany June 23, 1933 3 Claims. (01. 260-91) The present invention relates to water-insol- (2) The diazo solution prepared from 20.6 kilos uble azo-dyestuifs; more particularly it relates of l-amino-2-nitro-4-benzotrifiuoride is comto dyestuffs of the following general formula: bined with a cold aqueous solution of 17.8 kilos NOz of aceto-acetic anilide and 13 kilos of caustic ,5 soda solution. In order to accelerate the reaction, sodium acetate is advantageously added to the mixture. When the coupling is finished, the

dyestufi is filtered by suction, washed. and dried.

wherein R means the radical of a Z-hydroxy- It forms a yellow powder and corresponds to the naphthalene or of a compound containing a -Cl-I2-CO-group by means of which it is caformula:

pable of being combined with diazo compounds, N01 such as a pyrazolone or an acyl acetic arylide.

We have. found, that technically valuable pig- -O ment dyes are obtainable by coupling in sub- L stance or on a substratum the diazo compound of CHPC 1P0 O 15 l -amino-2-nitro-4-benzotrifluoride with a 2-hydroxynaphthalene, an acyl acetic arylide or a pyrazolone derivative containing groups en- Instead Of aceto-acetic anilide other 8Cyl acetic dering the dyestuffs soluble in water, such as sulalylides may be usedionic r carboxylie acid, groups, (3) The diazo solution prepared from 20.6 kilos The new dyestuffs are distinguished by a good of 1-amino-2-nitro-4-benzotrifiuoride is run into fastness to oils and a very good fastness to light. a cold finely divided suspension, prepared by dis- As regards the fastness to light they surpass the solving 18 kilos of l-phenyl-3-methyl-5-pyrazorim-dyestuffs described in j Patent lone in dilute caustic soda solution and precipi- 25 551,882, and obtainable by coupling diazotized mu with l t minera1aci In order t m ubstituted y @1110 celerate the coupling, sodium acetate is added to me In t0 the ammo group Wlth the mixture. The dyestuif is filtered by suction,

hydroxynaphthoic acid aryndes' washed and driedit forms an oran ge powder The following examples serve to illustrate the invention, but they are not intended to limit it and corresponds to the formula" V 30 thereto.

. (1) The diazo solution prepared from 20.6 kilos of 1-amino-2-nitro4=-benzotrifiuoride is run,

while stirring, into an ice-cold finely divided suspension of 15 kilos of beta-naphthol in the pres- 35 once of sodium acetate. The precipitated dye- N stuff is filtered, pressed and dried. It forms an N01 orange-red powder of good fastness to oils and f very good fastness to light. The dyestuif has the Hao-c--oH-N==N CF; 40 40 following formula.

N02 1 Instead of methylphenylpyrazolone other pyrazolone derivatives may be used. as coupling com- 0H ponents. 45

The following dyestufis, among others, are capable of production in accordance with this invention:

Diazo compound from- Combined withw 6-chlot0-2-naphthol- Orange. d 8-chloro-2-naphtho1- Yellowish orange.

Acetoacetic-o-clilo o-an Yellow. Acetoacetic-m-xylidid Greenish yellow. Benzoylacetie anilide Yellow. Benzoylacetic-o-chloro anilide 1130. O.

Benzoylacetic-m-nitram ide. Benzoylacetic l-amino-2-methoxy- Do.

wherein R means the radical of a Z-hydroxynaphthalene or of a compound containing a 2. The water-insoluble azo-dyestuff of the following formula:

being, when dry, an orange-red powder and yielding, when mixed with a substratum,

fastness to light.

3. The water-insoluble lowing formula:

when mixed with a good fastness to oils and very good fastness to light.

HANS HEYNA. HANS HUBER.

azo-dyestufi of the fol- 

